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Enantioselective Synthesis of (−)-Englerins A and B

Authors

  • Kian Molawi,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
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  • Nicolas Delpont,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
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  • Antonio M. Echavarren Prof.

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
    2. Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcel⋅li Domingo s/n, 43007 Tarragona (Spain), Fax: (+34) 977-920-225
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  • We thank the MICINN (CTQ2007-60745/BQU and Consolider Ingenio 2010, grant CSD2006-0003), the AGAUR (2009 SGR 47), and the ICIQ Foundation for financial support. We also thank E. Escudero-Adán and Dr. J. Benet-Buchholz (X-ray diffraction unit, ICIQ) for the X-ray structure determination of 8 b and 19, as well as Dr. Eloísa Jiménez-Núñez for helpful discussions.

Abstract

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All that glitters is gold: The total synthesis of the natural enantiomers of englerins A and B has been completed using a gold-catalyzed stereoselective domino alkyne/alkene/carbonyl cyclization of an enyne with an unprotected alcohol group at a stereogenic allylic position (see scheme; TES=triethylsilyl).

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